Premium
An Expeditious Synthesis of Chiral 1,2,4‐Oxadiazole Peptidomimetics from Heteroaroyl Monopeptides
Author(s) -
Purushotham Nikil,
Poojary Boja
Publication year - 2018
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201801921
Subject(s) - peptidomimetic , oxadiazole , chemistry , aryl , amide , combinatorial chemistry , amino acid , yield (engineering) , organic chemistry , peptide , materials science , biochemistry , alkyl , metallurgy
Amino acid derived amide bond bioisosteric peptidomimetics, such as 1,2,4‐oxadiazoles are generally prepared by two‐step processes as demonstrated well in the literature. There have been no reports on the synthesis of 1,2,4‐oxadiazoles from heteroaroyl peptides in a single step to date. In our work, 1,2,4‐oxadiazole peptidomimetics were synthesized efficiently via one‐pot cyclodehydration of O ‐acyl amidoximes engendered in situ, from heteroaroyl monopeptides and aryl or benzyl amidoximes with up to 93% yield. The process utilized DCC as the activating agent and did not considerably affect the conversion with the variation of amidoximes or monopeptides. Hence, the process could be useful in the design and synthesis of novel 1,2,4‐oxadiazole peptidomimetic based therapeutics.